Luxury Vacation Home Rentals on Anna Maria Island

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach, Bradenton Beach, & right Off Island, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Properties Available 42 properties available
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom
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La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $1,100.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (8)
Welcome to Hangin’ on Hammock!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Tucked along a quiet stretch on the north end of Anna Maria Island, this home blends easy island living with space to gather, unwind, and enjoy the water. Fresh paint, u
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Hangin on Hammock
Hangin on Hammock
Anna Maria Pet Friendly
$380.00 - $1,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
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Family Tides - B
Family Tides - B
Bradenton Beach
$280.00 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4 (1)
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
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Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$250.00 - $740.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
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Sunset Margarita
Sunset Margarita
Off Island Pet Friendly
$210.00 - $520.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)
Welcome to Cortez Dock & Dine!On Florida’s Gulf Coast (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A rare waterfront escape blending Old Florida charm with modern coastal living.Please note: Boat not included with rental. For more information about boat rental
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Cortez Dock & Dine
Cortez Dock & Dine
Off Island Pet Friendly
$190.00 - $700.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere calm meets connection, Serenity Now offers spacious living, modern comforts, and a private backyard oasis with a heated pool. Thoughtfully designed for ease and bal
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Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$380.00 - $1,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (12)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
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Tern Key
Tern Key
Anna Maria
$900.00 - $2,550.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceThoughtfully redesigned for simplicity and comfort, On Turtle Time blends the charm of an island cottage with the ease of modern living. Inside, natural light filt
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On Turtle Time
On Turtle Time
Holmes Beach
$250.00 - $800.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (5)
Welcome to Happy Ours!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.JUST RELAUNCHED AS A RENTAL and UNDER NEW MANAGEMENT! Experience Happy Ours — a rare direct beachfront retreat tucked along Magnolia Avenue on Anna
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Happy Ours
Happy Ours
Anna Maria
$780.00 - $2,980.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Welcome to Hidden Palms!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency*New & Improved Photos COMING SOON*The SpaceTucked into a quiet Holmes Beach neighborhood, this elevated island retreat invites you to slow down and settle into the rhythm of island lif
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Hidden Palms
Hidden Palms
Holmes Beach
$300.00 - $825.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
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Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$260.00 - $760.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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